CN108840802B - Synthesis method of intermediate 4-aminophenylethanol - Google Patents
Synthesis method of intermediate 4-aminophenylethanol Download PDFInfo
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- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- B01J37/344—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation of electromagnetic wave energy
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Abstract
The invention discloses a method for synthesizing an intermediate 4-aminophenylethanol, methanol and Pt-SnO2C, hydrazine hydrate, p-nitrophenyl alcohol, NaOH, SnCl2·2H2O, ethylene glycol, carbon black, H2PtC16The synthesis process of the invention adopts p-nitroacetophenol and hydrazine hydrate as catalysts Pt-SnO as main raw materials2Performing reduction reaction under the action of/C to obtain 4-aminophenylethanol; the reduction reaction selects low-cost self-made Pt-SnO2the/C is a catalyst for reducing the nitrobenzene ethanol by the hydrazine hydrate, the reaction condition is mild, the catalytic efficiency is high, and the purity and the yield of the product reach ideal effects.
Description
Technical Field
The invention relates to a synthetic method of an intermediate 4-aminophenylethanol, belonging to the field of chemical synthesis.
Background
4-Aminophenylethanol (4-amino phenyl alcohol) CAS: 104-10-9 is an important medical intermediate, can be used for synthesizing p-hydroxyphenylethanol, and further synthesizing medicaments such as metoprolol, salidroside, betaxolol and the like, other perfumes and organic synthesis intermediates. Aiming at the problems of large amount of ortho-isomer, complex synthesis process and low total yield of products in the process of preparing the p-aminophenylethanol by the traditional phenethyl alcohol synthesis method, the synthesis method of the 4-aminophenylethanol mainly comprises two types according to different raw materials, namely, taking p-nitrophenylacetic acid as a raw material and taking beta-phenethyl alcohol as a raw material. In both methods, p-nitrophenyl alcohol is obtained through reaction, and then 4-aminophenyl alcohol is obtained through reduction reaction. However, the reaction steps are numerous, so that the equipment investment cost is increased in the industrial production, and the ortho-isomer is generated in the nitration reaction, so that the total yield of the p-aminophenylethanol is greatly reduced, and the industrialization pace of the p-aminophenylethanol is hindered. Therefore, the industrial production method which explores a new 4-aminophenylethanol synthesis process, is easy to control reaction conditions, has fewer steps, high total yield and low production cost has practical significance.
Disclosure of Invention
The invention aims to provide a synthesis method of an intermediate 4-aminophenylethanol, which can catalyze the reduction reaction of p-nitrophenylethanol and hydrazine hydrate under optimized conditions and has higher product yield.
A synthetic method of an intermediate 4-aminophenylethanol is characterized by comprising the following steps:
step 1, adding 10ml of 0.1M hydrochloric acid solution with concentration, 500ml of methanol and 2g of catalyst Pt-SnO into a 1000ml three-neck flask provided with a thermometer, a mechanical stirrer and a reflux condenser2Heating to 68 ℃;
step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 75g of hydrazine hydrate, heating for reflux reaction, wherein the reflux temperature is 68 ℃;
step 3, monitoring the reaction by thin layer chromatography until the raw material point disappears, cooling and filtering to remove the components in the reaction mixture
Catalyst, distilling and recovering methanol under normal pressure;
and 4, cooling the mixed system to 20 ℃, adding a proper amount of water and a small amount of NaOH solution, freezing, filtering, and drying in vacuum to obtain the white 4-aminophenylethanol.
The Pt-SnO2The preparation method of the/C catalyst comprises the following steps:
step 1, adding 0.2g SnCl2·2H2Ultrasonically mixing O and 50ml of ethylene glycol for 0.5h, adding 5ml of deionized water, ultrasonically mixing for 5min, and performing microwave for 10 min;
step 2, fully and uniformly mixing the prepared mixed solution with 2g of carbon black by ultrasonic waves, stirring overnight, carrying out suction filtration, and carrying out vacuum drying at 80 ℃ for 12 hours to obtain SnO2a/C composite carrier;
step 3, to a 100ml beaker containing 25ml of ethylene glycol, 10ml of a solution containing 0.001mol H was added2PtC16Adding the prepared SnO into the ethylene glycol solution2Performing ultrasonic dispersion on the/C composite carrier for 30 min;
step 4, after uniform dispersion, dropwise adding a 0.1M KOH glycol solution, adjusting the pH =10 of the solution, and continuing ultrasonic dispersion for 30min to fully and uniformly disperse the mixture;
step 5, placing the mixed slurry into a microwave oven, heating for 20s by using microwaves, stopping lOs, repeating for 6 times, taking out the slurry, cooling, filtering, washing with distilled water for three times until no Cl exists-Vacuum drying at 80 deg.c for 12 hr to obtain Pt-SnO2a/C catalyst.
Has the advantages that: the invention provides a method for synthesizing an intermediate 4-aminophenylethanol, namely p-nitroanisole and hydrazine hydrate in a catalyst Pt-SnO2and/C, carrying out reduction reaction to obtain the 4-aminophenylethanol. Under neutral or weakly alkaline conditions, Pt-SnO2The method comprises the steps of firstly, Pt catalyzes hydrazine to lose electrons to decompose the hydrazine into nitrogen and active hydrogen ions, then, p-nitroacetophenol obtains electrons under the action of the active hydrogen ions, and the product is obtained through three-step reduction reaction
The substance aminophenylethanol. The aromatic amine is prepared by reducing nitro group with hydrazine hydrate as a reducing agent, and has the advantages of mild reaction condition, high reaction speed and reaction
Obvious reaction phenomenon, high reduction yield, small equipment investment, simple operation, no waste residue, environmental protection and the like. However, hydrazine hydrate is slowly dripped into the reaction liquid, and the temperature rise process is also in a step-type manner, because the dripping is too fast or the temperature rise is too violent, the active hydrogen generated by the decomposition of the hydrazine hydrate is easy to combine with the nitro compound to escape as hydrogen, the dosage of the hydrazine hydrate is increased, and the reduction reaction adopts low-cost self-made Pt-SnO2the/C is a catalyst for reducing the nitrobenzene ethanol by the hydrazine hydrate, the reaction condition is mild, the catalytic efficiency is high, and the purity and the yield of the product reach ideal effects.
Detailed Description
Example 1
A synthetic method of an intermediate 4-aminophenylethanol is characterized by comprising the following steps:
step 1, adding 10ml of 0.1M hydrochloric acid solution with concentration, 500ml of methanol and 2g of catalyst Pt-SnO into a 1000ml three-neck flask provided with a thermometer, a mechanical stirrer and a reflux condenser2Heating to 68 ℃;
step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 75g of hydrazine hydrate, heating for reflux reaction, wherein the reflux temperature is 68 ℃;
step 3, monitoring the reaction by thin layer chromatography until the raw material point disappears, cooling and filtering to remove the components in the reaction mixture
Catalyst, distilling and recovering methanol under normal pressure;
and 4, cooling the mixed system to 20 ℃, adding a proper amount of water and a small amount of NaOH solution, freezing, filtering, and drying in vacuum to obtain the white 4-aminophenylethanol.
The Pt-SnO2The preparation method of the/C catalyst comprises the following steps:
step 1, adding 0.2g SnCl2·2H2Ultrasonically mixing O and 50ml of ethylene glycol for 0.5h, adding 5ml of deionized water, ultrasonically mixing for 5min, and performing microwave for 10 min;
step 2, fully and uniformly mixing the prepared mixed solution with 2g of carbon black by ultrasonic waves, stirring overnight, carrying out suction filtration, and carrying out vacuum drying at 80 ℃ for 12 hours to obtain SnO2a/C composite carrier;
step 3, to a 100ml beaker containing 25ml of ethylene glycol, 10ml of a solution containing 0.001mol H was added2PtC16Adding the prepared SnO into the ethylene glycol solution2Performing ultrasonic dispersion on the/C composite carrier for 30 min;
step 4, after uniform dispersion, dropwise adding a 0.1M KOH glycol solution, adjusting the pH =10 of the solution, and continuing ultrasonic dispersion for 30min to fully and uniformly disperse the mixture;
step 5, placing the mixed slurry into a microwave oven, heating for 20s by using microwaves, stopping lOs, repeating for 6 times, taking out the slurry, cooling, filtering, washing with distilled water for three times until no Cl exists-Vacuum drying at 80 deg.c for 12 hr to obtain Pt-SnO2a/C catalyst.
Example 2
Step 2, adding 80g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 75g of hydrazine hydrate, heating and carrying out reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 3
Step 2, adding 60g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 75g of hydrazine hydrate, and heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 4
Step 2, adding 50g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 75g of hydrazine hydrate, and heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 5
Step 2, adding 40g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 75g of hydrazine hydrate, and heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 6
Step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 65g of hydrazine hydrate, and heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 7
Step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 55g of hydrazine hydrate, heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 8
Step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 45g of hydrazine hydrate, heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 9
Step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 35g of hydrazine hydrate, heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Example 10
Step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 25g of hydrazine hydrate, heating for reflux reaction, wherein the reflux temperature is 68 ℃; the rest of the procedure was the same as in example 1.
Comparative example 1
The difference from embodiment 1 is that: synthesis of intermediates step 1, the same amount of Pt was used as the catalyst, and the rest of the procedure was exactly the same as in example 1.
Comparative example 2
The difference from embodiment 1 is that: in the step 1 of synthesizing the intermediate, the catalyst Pt-SnO is not added2The rest of the procedure was exactly the same as in example 1.
Comparative example 3
The difference from embodiment 1 is that: in the step 1 of catalyst synthesis, SnCl is not added any more2·2H2O, the rest of the procedure is exactly the same as in example 1.
Comparative example 4
The difference from embodiment 1 is that: synthesis of the catalyst step 1, with an equal amount of FeCl2·4H2O substituted SnCl2·2H2O, the rest of the procedure is exactly the same as in example 1.
Comparative example 5
The difference from embodiment 1 is that: in the catalyst synthesis step 2, the prepared mixed solution and 2g of white carbon black are fully and uniformly mixed by ultrasonic, and the rest steps are completely the same as those in the example 1.
Comparative example 6
The difference from embodiment 1 is that: in the catalyst synthesis step 2, the mixed solution prepared above and 2g of kaolin were thoroughly and uniformly mixed by ultrasound, and the rest of the steps were exactly the same as in example 1.
Comparative example 7
The difference from embodiment 1 is that: synthesis of catalyst step 2, SnCl2·2H2O and carbon black in a mass ratio of 1: 1; the rest of the procedure was exactly the same as in example 1.
Comparative example 8
The difference from embodiment 1 is that: synthesis of catalyst step 2, SnCl2·2H2O and carbon black in a mass ratio of 10: 1; the rest of the procedure was exactly the same as in example 1.
Comparative example 9
The difference from embodiment 1 is that: catalyst synthesis step 4, the pH of the solution was adjusted =7, and the rest of the procedure was exactly the same as in example 1.
Comparative example 10
The difference from embodiment 1 is that: catalyst synthesis step 4, the pH of the solution was adjusted =3, and the rest of the procedure was exactly the same as in example 1.
The results of the reactions under different conditions in the examples and the comparative examples are shown in the table
| 4-Aminophenylethanol yield/%) | |
| Example 1 | 99.7 |
| Example 2 | 81.0 |
| Example 3 | 74.3 |
| Example 4 | 66.3 |
| Example 5 | 70.2 |
| Example 6 | 60.7 |
| Example 7 | 54.5 |
| Example 8 | 67.3 |
| Example 9 | 61.6 |
| Example 10 | 53.9 |
| Comparative example 1 | 41.9 |
| Comparative example 2 | 35.4 |
| Comparative example 3 | 48.5 |
| Comparative example 4 | 50.2 |
| Comparative example 5 | 57.1 |
| Comparative example 6 | 40.7 |
| Comparative example 7 | 49.0 |
| Comparative example 8 | 59.1 |
| Comparative example 9 | 61.0 |
| Comparative example 10 | 48.5 |
The experimental result shows that the catalyst has good catalytic effect on the reduction reaction of the p-nitroacetophenol and the hydrazine hydrate, and when the reaction condition is fixed, the higher the yield of the intermediate is, the better the catalytic performance is, and otherwise, the worse the catalytic performance is; the mass ratio of the p-nitroanisole to the hydrazine hydrate is 5: 4, other ingredients are fixed, the synthesis effect is best, and the difference from the example 1 is that the yield is not as high as that of the example 1 although the dosage and the proportion of main raw materials of the paranitroanisole and the hydrazine hydrate are changed from the example 2 to the example 10; comparative examples 1 to 2 No longer added Pt-SnO catalyst2The Pt is used for replacing the catalyst/C, and other steps are completely the same, so that the product yield is obviously reduced, which indicates that the composite catalyst has great influence on the reaction product; comparative examples 3 to 4 use equal amounts of FeCl2·4H2O substituted SnCl2·2H2O, the effect is still not good, which shows that SnCl2·2H2The synthetic component effect of the O as the carrier is better; comparative examples 5 to 8 were prepared by substituting carbon black with white carbon black and kaolin, respectively, and varying SnCl2·2H2The mass ratio of O to carbon black is obviously poor, which shows that the carbon black carrier and the proportion of the carbon black carrier have great influence on the catalytic performance; in comparative examples 9 to 10, the PH of the mixed system after the reaction was lowered, the activity of the catalyst was changed, the reaction effect was significantly deteriorated, and the product yield was significantly reduced; therefore, the catalyst has excellent catalytic effect on the synthesis reaction of the intermediate 4-aminophenylethanol.
Claims (1)
1. A synthetic method of an intermediate 4-aminophenylethanol is characterized by comprising the following steps:
step 1, adding a thermometer, mechanically stirring,A1000 ml three-neck flask with a reflux condenser was charged with 10ml of 0.1M hydrochloric acid solution, 500ml of methanol and 2g of Pt-SnO catalyst2Heating to 68 ℃;
step 2, adding 100g of p-nitrophenyl alcohol into the ethanol solution, adjusting the pH to be =7 by using 30% NaOH, uniformly stirring, slowly dropwise adding 75g of hydrazine hydrate, heating for reflux reaction, wherein the reflux temperature is 68 ℃;
step 3, monitoring the reaction by thin layer chromatography until the raw material point disappears, cooling and filtering to remove the components in the reaction mixture
Catalyst, distilling and recovering methanol under normal pressure;
step 4, cooling the mixed system to 20 ℃, adding a proper amount of water and a small amount of NaOH solution, freezing, filtering, and drying in vacuum to obtain white 4-aminophenylethanol;
the Pt-SnO2The preparation method of the/C catalyst comprises the following steps:
step 1, adding 0.2g SnCl2·2H2Ultrasonically mixing O and 50ml of ethylene glycol for 0.5h, adding 5ml of deionized water, ultrasonically mixing for 5min, and performing microwave for 10 min;
step 2, fully and uniformly mixing the prepared mixed solution with 2g of carbon black by ultrasonic waves, stirring overnight, carrying out suction filtration, and carrying out vacuum drying at 80 ℃ for 12 hours to obtain SnO2a/C composite carrier;
step 3, to a 100ml beaker containing 25ml of ethylene glycol, 10ml of a solution containing 0.001mol H was added2PtC16Adding the prepared SnO into the ethylene glycol solution2Performing ultrasonic dispersion on the/C composite carrier for 30 min;
step 4, after uniform dispersion, dropwise adding a 0.1M KOH glycol solution, adjusting the pH =10 of the solution, and continuing ultrasonic dispersion for 30min to fully and uniformly disperse the mixture;
step 5, placing the mixed slurry into a microwave oven, heating for 20s by using microwaves, stopping for 10s, repeating for 6 times, taking out the slurry, cooling, filtering, washing with distilled water for three times until no Cl exists-Vacuum drying at 80 deg.c for 12 hr to obtain Pt-SnO2a/C catalyst.
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| CN1844324A (en) * | 2005-04-06 | 2006-10-11 | 中国石油天然气股份有限公司 | Process for preparing composite carbon carrier noble metal dehydrogenation catalyst |
| CN104525194A (en) * | 2014-12-30 | 2015-04-22 | 中国石油天然气股份有限公司 | Catalyst used for preparing isobutene through isobutane dehydrogenation and preparation method and application thereof |
| CN104892427A (en) * | 2015-05-25 | 2015-09-09 | 河南师范大学 | Preparation method of p-aminophenylethylamine |
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